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Sigma-Aldrich

(DHQD)2PHAL

greener alternative

≥95%

Sinonimo/i:

Hydroquinidine 1,4-phthalazinediyl diether

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1 G
CHF 193.00

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1 G
CHF 193.00

About This Item

Formula empirica (notazione di Hill):
C48H54N6O4
Numero CAS:
Peso molecolare:
778.98
Beilstein:
5475678
Numero MDL:
Codice UNSPSC:
12352005
ID PubChem:
NACRES:
NA.22

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Saggio

≥95%

Stato

powder

Attività ottica

[α]22/D −262°, c = 1.2 in methanol

Punteggio alternativa più verde

old score: 5
new score: 3
Find out more about DOZN™ Scoring

Caratteristiche più verdi

Waste Prevention
Less Hazardous Chemical Syntheses
Safer Solvents and Auxiliaries
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

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Punto di fusione

160 °C (dec.) (lit.)

Categoria alternativa più verde

Stringa SMILE

CC[C@H]1CN2CCC1CC2[C@@H](Oc3nnc(O[C@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c8ccccc38)c9ccnc%10ccc(OC)cc9%10

InChI

1S/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30-,31-,32-,43+,44+,45-,46-/m0/s1
YUCBLVFHJWOYDN-HVLQGHBFSA-N

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Descrizione generale

(DHQD)2PHAL is a dimer that can be used as a chiral amine catalyst for asymmetric halogenations.[1][2]

(DHQD)2PHAL is a modified cinchona alkaloid derivative mainly used as a ligand for enantioselective catalysis.[3]
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Less Hazardous Chemical Syntheses”, "Safer Solvents and Auxiliaries" and “Inherently Safer Chemistry for Accident Prevention”. Click here to view its DOZN scorecard.

Applicazioni

(DHQD)2PHAL may be used as ligand for:
  • Osmium trioxide catalyzed asymmetric dihydroxylation of olefins.[3]
  • Palladium catalyzed Suzuki-Miyaura coupling of aryl/heteroaryl halides with aryl boronic acids in aqueous medium and in the absence of phosphine/organic solvent.[4]
  • Copper(I)-catalyzed azide-alkyne cycloaddition reaction to synthesize 1,2,3-triazoles in water.[5]
Hydroquinidine 1,4-phthalazinediyl diether [(DHQD)2PHAL] can be used:
  • As a ligand for Sharpless asymmetric dihydroxylation.[6]
  • For enantioselective α-fluorination of carbonyl compounds.[7]

Note legali

Sold under license from Rhodia Pharma Solutions.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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I clienti hanno visto anche

Chemical Fixation of Carbon Dioxide Co-Catalyzed by a Combination of Schiff Bases or Phenols and Organic Bases.
Shen YM, et al.
European Journal of Organic Chemistry, 2004(14), 3080-3089 (2004)
Tetrahedron Asymmetry, 16, 3913-3913 (2005)
(DHQD) 2 PHAL ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition reactions in water at room temperature.
Ali AA, et al.
Royal Society of Chemistry Advances, 4(110), 64388-64392 (2014)
Synthesis of enantiomerically enriched Baylis--Hillman alcohols from their acetates: combination of kinetic resolution during the salt formation with (DHQD) 2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate
Kim J, et al.
Tetrahedron Letters, 43, 9141-9146 (2002)
Monomeric Cinchona Alkaloid-Based Catalysts for Highly Enantioselective Bromolactonisation of Alkynes
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Chemistry?A European Journal , 22, 18601-18607 (2016)

Contenuto correlato

The Sharpless Lab pursues useful new reactivity and general methods for selectively controlling chemical reactions.

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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